4-Hy­droxy-N′-(3-nitro­benzyl­idene)benzohydrazide

Jin-Long Hou

doi:10.1107/S1600536812014778

. 2012 Apr 13;68(Pt 5):o1352. doi: 10.1107/S1600536812014778

4-Hydroxy-N′-(3-nitrobenzylidene)benzohydrazide

Jin-Long Hou ^a,^*

PMCID: PMC3344485 PMID: 22590247

Abstract

The title compound, C₁₄H₁₁N₃O₄, was obtained by a condensation reaction between 3-nitrobenzaldehyde and 4-hydroxybenzohydrazide. The whole molecule is approximately planar, with a dihedral angle of 9.2 (3)° between the benzene rings. The molecule displays an E conformation about the C=N bond. In the crystal, molecules are linked via N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds, generating sheets parallel to the bc plane.

Related literature

For the biological properties of hydrazone compounds, see: Cukurovali et al. (2006 ▶); Karthikeyan et al. (2006 ▶); Kucukguzel et al. (2006 ▶). For related hydrazone compounds, see: Hou (2009 ▶); Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Zhang et al. (2009 ▶); Khaledi et al. (2008 ▶). For standard bond lengths, see: Allen et al. (1987) ▶.

Experimental

Crystal data

C₁₄H₁₁N₃O₄
M _r = 285.26
Monoclinic,
a = 8.018 (2) Å
b = 11.156 (2) Å
c = 14.389 (2) Å
β = 91.773 (2)°
V = 1286.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.21 × 0.20 × 0.17 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.977, T _max = 0.981
9218 measured reflections
2386 independent reflections
2020 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.108
S = 1.10
2386 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812014778/qm2061sup1.cif

e-68-o1352-sup1.cif^{(15.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014778/qm2061Isup2.hkl

e-68-o1352-Isup2.hkl^{(117.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812014778/qm2061Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.90 (1)	2.49 (2)	3.0406 (18)	120 (1)
N2—H2A⋯O4ⁱⁱ	0.90 (1)	2.32 (1)	3.0360 (17)	137 (2)
O4—H4⋯N1ⁱⁱⁱ	0.82	2.63	3.0495 (17)	114
O4—H4⋯O3ⁱⁱⁱ	0.82	2.08	2.8929 (16)	173

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

This project was supported by the Research Foundation of the Education Bureau of Heilongjiang Province, China (grant No. 11521312).

supplementary crystallographic information

Comment

Hydrazones derived from the condensation reactions of hydrazides with aldehydes show excellent biological properties (Cukurovali et al., 2006; Karthikeyan et al., 2006; Kucukguzel et al., 2006). In the last few years, a great deal of hydrazone compounds have been reported for their crystal structures see (Hou, 2009; Mohd Lair et al., 2009; Fun et al., 2008; Zhang et al., 2009; Khaledi et al., 2008). In this paper, the title new compound, derived from the condensation reaction of 3-nitrobenzaldehyde and 4-hydroxybenzohydrazide was synthesized and structurally characterized.

The molecular structure of the compound is shown in Fig. 1. The whole molecule of the compound is approximately coplanar, with the dihedral angle between the mean planes through the two benzene rings of 9.2 (3)°. The molecule displays an E configuration about the C=N bond. All the bond lengths are within normal ranges (Allen et al., 1987). In the crystal, molecules are linked via N–H···O hydrogen bonds (Table 1), generating two-dimensional sheets (Fig. 2).

Experimental

3-Nitrobenzaldehyde (1.0 mmol, 151 mg) and 4-hydroxybenzohydrazide (1.0 mmol, 152 mg) were mixed and refluxed with stirring for two hours. Yellow single crystals were formed after slow evaporation of the solution in air for a week.